N,N'-diaryl-N-alkylureas and method of use

Abstract

An N,N-diaryl-N-alkylurea having the formula ##STR1## wherein R 1 , R 2 , R 3 and R 4 are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido, substituted phenoxy and substituted pyridyloxy groups wherein the substituent is any one of halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido; and R 5 is selected from the group consisting of alkyl, alkenyl, haloalkyl, haloalkenyl, hydroxyalkyl, hydroxylalkenyl, acetoxyalkyl, acetoxyalkenyl, mercaptoalkyl, and mercaptoalkenyl, wherein the alkyl or alkenyl group in each alkyl- or alkenyl-containing moiety has from 3 to 6 carbon atoms; X is oxygen or sulfur; and agriculturally acceptable salts thereof. Also disclosed is an herbicidal composition and method of treating weeds.

What is claimed is: 
     
       1. An N,N'-diaryl-N-alkylurea having the formula ##STR21## wherein R 1 , R 2 , R 3  and R 4  are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido, substituted phenoxy and substituted pyridyloxy groups wherein the substituent is any one of halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido; and R 5  is selected from the group consisting of alkyl, alkenyl, haloalkyl, haloalkenyl, hydroxyalkyl, hydroxylalkenyl, acetoxyalkyl, acetoxyalkenyl, mercaptoalkyl, and mercaptoalkenyl, wherein the alkyl or alkenyl group in each alkyl- or alkenyl-containing moiety has from 3 to 6 carbon atoms; and   X is oxygen or sulfur.   
     
     
       2. The compound of claim 1 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-cyano, R 5  is CH 2  CH═CH 2  and X is sulfur. 
     
     
       3. The compound of claim 1 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-cyano, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       4. The compound of claim 1 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-fluoro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       5. The compound of claim 1 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 3-nitro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       6. The compound of claim 1 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 3-fluoro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       7. A herbicidal composition which comprises an herbicidally effective amount of an N,N'-diaryl-N-alkylurea having the formula ##STR22## wherein R 1 , R 2 , R 3  and R 4  are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido, substituted phenoxy and substituted pyridyloxy groups wherein the substituent is any one of halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido; and R 5  is selected from the group consisting of alkyl, alkenyl, haloakyl, haloakenyl, hydroxyalkyl, hydroxylalkenyl, acetoxyalkyl, acetoxyalkenyl, mercaptoalkyl, and mercaptoalkenyl, wherein the alkyl or alkenyl group in each alkyl- or alkenyl-containing moiety has from 3 to 6 carbon atoms; and   X is oxygen or sulfur; and an inert diluent carrier therefor.     
     
     
       8. The composition of claim 7 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-cyano, R 5  is CH 2  CH═CH 2  and X is sulfur. 
     
     
       9. The composition of claim 7 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-cyano, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       10. The composition of claim 7 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-fluoro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       11. The composition of claim 7 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 3-nitro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       12. The composition of claim 7 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 3-fluoro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       13. A method for controlling undesirable weed pests which comprises applying to the locus where control is desired an herbicidally effective amount of an N,N'-diaryl-N-alkylurea having the formula ##STR23## wherein R 1 , R 2 , R 3  and R 4  are the same or different and are selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido, substituted phenoxy and substituted pyridyloxy groups wherein the substituent is any one of halogen, cyano, trifluoromethyl, trifluoromethylthio, trifluoromethyl thionyl, trifluoromethane sulfonyl, sulfonamido; and R 5  is selected from the group consisting of alkyl, alkenyl, haloalkyl, haloalkenyl, hydroxyalkyl, hydroxylalkenyl, acetoxyalkyl, acetoxyalkenyl, mercaptoalkyl, and mercaptoalkenyl, wherein the alkyl or alkenyl group in each alkyl- or alkenyl-containing moiety has from 3 to 6 carbon atoms; and   X is oxygen or sulfur.   
     
     
       14. The method of claim 13 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-cyano, R 5  is CH 2  CH═CH 2  and X is sulfur. 
     
     
       15. The method of claim 13 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-cyano, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       16. The method of claim 13 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 4-fluoro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       17. The method of claim 13 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 3-nitro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen. 
     
     
       18. The method of claim 13 wherein R 1  is hydrogen, R 2  is 3-trifluoromethyl, R 3  is hydrogen, R 4  is 3-fluoro, R 5  is CH 2  CHClCH 2  CH 3  and X is oxygen.